Which is better to work at, small companies or big companies?

I’ve worked at companies ranging from 3 guys in a converted garage to a global, publicly traded company with 65,000 employees and everywhere in between, and the honest truth is that there’s no right or wrong answer to this question. It depends on the company, the individual, and the match between the two.

That said, there are some broad patterns that you should be aware of to make sure that you’re picking your moves carefully and don’t end up falling into the Zone Of Pain. What’s the Zone of Pain, you ask?? I’ll tell you in just a minute— but first, let’s get the basics out of the way…

THE BIG DIFFERENCE: HOW MANY HATS YOU WILL WEAR
In general, the main thing about big companies is that roles are much more rigidly defined. If you’re a graphic designer at a big company, all you will ever do is graphic design. Trying to do more than is in your job description will probably just piss people off. This can be a little frustrating if you’re one of those people (like me) who enjoys trying new things, but it’s also a good thing in that it forces you to really focus on getting really fucking good at one skillset.

At small companies you will probably get the opportunity to wear more than one hat. If you’re a graphic designer you might get asked to help out with marketing or putting together a big presentation for client/business partner. This is cool because you’ll get a chance to try out new things, but it can also be a bad thing in that you can get spread thin— and as I’ve said many times before, being a jack of all trades is NOT a good thing!

LET’S GET MORE SPECIFIC
The way I see it, we can basically sort all companies into FOUR categories based on their SIZE (big or small) and whether they are GOOD OR BAD at what they do. Each of these categories has its own unique pros and cons:

THE ZONE OF PAIN (small + bad)
My opinion of these companies should be pretty clear: no bueno!! Companies in the ZoP are small in all the wrong ways: they have limited resources, their management is a haphazard, disorganized mess, and they’re oftentimes struggling to just survive so there’s no job security.

Because they are shitty at what they do, you aren’t likely to learn much from one of these companies. And because they’re also small, you don’t even get the benefit of having a recognizable name on your resume.

As anyone who has been stuck there, I can tell you that the ZoP is like quicksand: once you’re in, it can be really fucking hard to get out (having a bad company on your resume makes good companies less likely to consider you, so it can turn into a “shit spiral“).

The majority of jobs in music, action sports or entertainment fall into this category btw. If you don’t believe me, ask anyone who’s worked in the industry.

THE B-TEAM (big + bad)
When people talk about a “lame corporate job,” these are the kind of companies they’re talking about. However, I’m a lot more optimistic about these jobs and you should be too.

Yeah, these might not be the sexiest companies in the world and the work may be a little uninspiring, but I really cannot underestimate the value of having a big, recognizable name on your resume (read my earlier post about job titles for more detail on this). This will open a lot of doors for you in the future— doors that will be closed to all the “cool” kids who are stuck in the ZoP because they turned up their noses at these “lame corporate jobs.”

Also, you’ll learn a lot at these jobs— maybe not the very BEST way of doing things, but you’ll at least learn how huge companies do things, and that’s really valuable experience.

I know that the prospect of working at JC Penney or Olive Garden’s corporate office probably doesn’t sound super exciting, but if an opportunity like that ever comes your way, be smart and give it a second chance.

THE ELITE (small + good)
Think of these companies as a highly selective squad of commandos like the X-Men— they’re small, but they’re really damn good. It’s hard to get in, but after a couple years at one of these jobs you will be among the best in the world at what you do. Working shoulder to shoulder with other elites will hone your skills to a razor edge.

The downsides are less name value on your resume and oftentimes limited room for advancement (when there’s only 20 people at the company there aren’t a lot of open seats), but that can be a worthwhile tradeoff for the ninja-level skills you’ll develop at one of these firms.

Also, when people DO recognize the name of the company, it will probably mean a lot to them— “Oh shit, you worked for THEM? OK, we definitely need to bring you in for an interview.”

THE BIG LEAGUES (big + good)
These companies are household names that are the global leaders in their industry. They are super highly respected, and for good reason: it’s incredibly fucking hard to be both good AND big. Most companies start to suck when they grow, but these companies keep their edge even as they scale— usually due to the leadership of a visionary founder/CEO (Jeff Bezos, Phil Knight, Bill Gates, etc).

Working at these companies is an incredible opportunity, because you will learn things here that you simply can’t learn anywhere else. For example, when I was at Abercrombie I was responsible for rolling out marketing campaigns to over 1,000 stores on three continents. Or working with P&G, we developed packaging for products that sold hundreds of millions of units a year. As you can imagine, it’s pretty fucking cool to work on things at that scale!

There are two main downsides to the big leagues:

Working at these companies is fucking HARD. They will push you further than you thought you could go and get you to do things that you thought were impossible— like when I had to get a billboard shipped from Ohio to Hong Kong in less than 24 hours (for the record, I pulled it off). So make sure you know what you’re signing up for.

It can make you a bit lazy if you get used to having the option of throwing money at problems. Drop $10k on rush fees to get something printed in time to make a deadline? No problem, that’s a drop in the bucket. You can see how this might develop some bad habits that get you in trouble at smaller companies (eg startups).

IN SUMMARY
Of course, in the real world things are rarely as tidy as I’ve made them look in this post so you’re going to have to do your own analysis to determine what the right move is for your career. I encourage you to apply this framework to the companies in your industry and/or in your city as you think about how to shape your career.